You probably can't afford a $38 million Ferrari, but isn't it fun to think about it?

No. 10 on the list is a Ferrari 250 GT Tour de France: the curvaceous hardtop progenitor of Ferrari's most memorable cars of the last century. Like so many of the highly collectible Ferrari's on this list, the TDF was entered as a race car multiple times, including the eponymous Tour de France and the Rome Grand Prix. Just because the TDF's price was lower then the others here, that doesn't mean it isn't worth a buck. It's the 50's model that sets the tone for the more desirable 60's models.

No. 9: 1998 McLaren F1 LMSold for: $13.8 million in 2015.

Of the classic cars that earn their keep the most in Monterey, only one isn't a Ferrari. But this McLaren F1 is hardly showroom-spec (or as off the lot as McLaren get): it started life as a road-going F1 before undergoing a conversion to the vaunted LM spec, including those models' bespoke V-12 and aero equipment. Was the new owner satisfied with the purchase? Likely, as the F1 LM was spotted more often on the roads of Monateray after the transaction.

There are so many variations to the lineage of the Ferrari 250 GT, and a collector pays dearly to own the exact one he wants. Of the 56 Scaglietti-built 250 GT's, only 37 had covered headlights, and this California Spider is among them. A bonus item most definitely included in the multi million-dollar price, is a rare and desirable hard top. You know, for when you want to take the weekend car and it starts to rain.

No. 7: 1957 Ferrari 250 Testa RossaSold for: $16.4 million in 2011

Diversity is one of the only characteristics separating the most exclusive cars, and this Ferrari Testa Rossa is rolling proof. When it sold for over $16 million in 2011, it set a new auction record—not just in the U.S., but the world over. Today, its "low" price tag likely reflects the sentiment of a nation coming out of recession—hey, even a billionaire has to eat—and the '57 Testa Rossa could become even more valuable while off the block.

Courtesy of Gooding and Co.

No. 6: 1962 Ferrari 250 GT SWB CoupeSold for: $16.5 million in 2015

What has a V-12, a 4-speed manual, disc brakes, and all of its paperwork in order? This 1962 Ferrari 250 GT, a short-wheelbase coupe, painted a gorgeous cerulean. It slips in just under the $17 million mark, in line with the average sale price for the vehicles with the highest price tags. In addition to having taken top honors at concours events in past years, the 250 GT is reported to have served as personal car of Mr. Bertone himself. Come prestigioso!

This Ferrari comes from an era when "California" evoked images of endless summer and drop-top weather: a dream for most of us. The lucky owner of the '61 250 GT California Spider is likely in a dream world of his own. Don't think of it as worth half as much as the 250 GT that sold for $38 million—envision this spectacular convertible as the smart-money investment.

No. 4: 1964 Ferrari 250 LM CoupeSold for: $17.6 million in 2015

Like some of the others in this cadre, this Ferrari 250 LM was coach-built by Scaglietti, adding to its prestige and inflating its worth. For some perspective, see below for how much a McLaren F1 sold for, just the same year. It's reported to be number 23 of 32 produced, making this list some-thing of a homecoming for a storied few Italian superheroes.

No.3: 1964 Ferrari 275 GTB/C SpecialeSold for: $26.4 million in 2014

What makes this 275 GTB different from some other fine Ferraris to command top dollar in Monterey? Like fine artwork, it's been cared for and preserved, and it belongs to a very prestigious and rare lineage. Oh, and because it took third at Le Mans in 1965. Try saying that about most modern garage-queen collector cars.

Until the sale of the 250 GTO Berlinetta, this '67 275 GTB soft-top held the record for most expensive sale of a non-race car in the United States. Anyone who puts down eight figures for an automobile should be able to dispense related trivia, like an explanation for the 275 GTB's seemingly unintelligible suffix (which stands for "North American Racing Team").

No. 1: 1962 Ferrari 250 GTO BerlinettaSold for: $38.1 million in 2014

Talk about pedigree: This particular 250 GTO Berlinetta made a name for itself as a competitor and a winner, before ever falling into the loving hands of collectors. With under 40 ever produced, it's no wonder that the 250s top this list—and it holds the record for the most expensive car to ever be sold at an auction, in Monterey or otherwise.